GB1396748A - 4-4-biphenylyl - butyramides - Google Patents

4-4-biphenylyl - butyramides

Info

Publication number
GB1396748A
GB1396748A GB3871272A GB3871272A GB1396748A GB 1396748 A GB1396748 A GB 1396748A GB 3871272 A GB3871272 A GB 3871272A GB 3871272 A GB3871272 A GB 3871272A GB 1396748 A GB1396748 A GB 1396748A
Authority
GB
United Kingdom
Prior art keywords
compounds
biphenylyl
reacting
reducing
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB3871272A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Boehringer Ingelheim Pharma GmbH and Co KG
Original Assignee
Dr Karl Thomae GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE2141926A external-priority patent/DE2141926A1/en
Priority claimed from DE2141925A external-priority patent/DE2141925A1/en
Priority claimed from DE2141927A external-priority patent/DE2141927A1/en
Application filed by Dr Karl Thomae GmbH filed Critical Dr Karl Thomae GmbH
Publication of GB1396748A publication Critical patent/GB1396748A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/58—One oxygen atom, e.g. butenolide
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1396748 4 - (4 - Biphenylyl) - butyric acid amides DR KARL THOMAE GmbH 18 Aug 1972 [20 Aug 1971 (3)] 38712/72 Heading C2C The invention comprises 4-(4-biphenylyl)- butyric acid amides of the Formula I wherein A is R 1 is halogen, H, NO 2 , NH 2 or CN with the proviso that where A is -CH 2 CH 2 CH 2 - R 1 is halogen; R 2 is H or halogen; and R 3 and R 4 each are H, C 1-5 alkyl optionally substituted by H or C 1 -alkoxy, or phenyl optionally substituted by halogen, OH, CF 3 , C 1 -alkyl or C 1 -alkoxy; or R 3 and R 4 together with the nitrogen atom to which they are attached form a 1-pyrrolidinyl, piperidino, morpholino or 1-piperazinyl group each of which may be substituted by C 1 -alkyl, and acid addition salts of these compounds which contain basic nitrogen atoms. The compounds are prepared by reacting compounds of the formula wherein A is -CHOH-CH 2 CH 2 -, X is OR, where R is alkyl, aryl or aralkyl, and A is -COCH 2 CH 2 - or -CH 2 CH 2 CH 2 -, X is O-CO-OR, O-CO-R or OR or halogen or OH with the proviso that X may not be OH unless A is CH 2 CH 2 CH 2 with compounds of the formula HNR 3 R 4 , and, if necessary, removing protecting groups from any protected amino groups present. Compounds in which A is -COCH 2 CH 2 - may also be prepared by reacting the corresponding 5-(4-biphenylyl)-2(3H)- furanones, obtained by treating the appropriate 4 - (4 - biphenylyl) - 4 - oxobutyric acids with acetic anhydride; with compounds of the formula HNR 3 R 4 , or by reducing the corresponding 4 - (4 - biphenylyl) - 4 - oxocrotonic acid amides. Compounds in which A is may also be made by reducing compounds in which A is .COCH 2 CH 2 , or by reducing a mixture of such compounds with the corresponding 1 - R 3 - 5 - (4 - biphenylyl) - 5 - hydroxy - 2- pyrrolidinones, or by reducing the corresponding 4-(4-biphenylyl)-4-oxocrotonic acid amides or 4- (4-biphenylyl)-4-hydroxy-crotonic acid amides, or by reacting the appropriate γ-(4-biphenylyl)- γ-butyrolactones with compounds of the formula NHR 3 R 4 . Compounds in which A is may also be obtained by reducing compounds in which A is -COCH 2 CH 2 or Compounds in which R 1 is NH 2 may be prepared by reducing the corresponding compounds of Formula I in which R 1 is NO 2 . 4 - (2<SP>1</SP>,3<SP>1</SP> - Dichloro - 4 - biphenylyl) - butyric acid chloride is obtained by reacting the acid with thionyl chloride. 4 - (2<SP>1</SP> - Fluoro - 4 - biphenylyl) - 4 - oxo - N- propylcrotonamide is obtained by the mixed anhydride of the acid with ethyl chloroformate with propylamine. 4 - (2<SP>1</SP> - Nitro - 4 - biphenylyl) - 4 - oxobutyric acid benzoic anhydride is made by reacting the acid with benzoyl chloride. 5 - (2<SP>1</SP> - Fluoro - 4 - biphenylyl) - 1 - ethyl - 5- hydroxy-2-pyrrolidinone is obtained by reacting γ - (4<SP>1</SP> - fluoro - 4 - biphenylyl)-γ-butyrolactone with ethylamine. Pharmaceutical compositions, suitable for oral, parenteral or rectal administration, contain the above novel compounds or pharmaceutically acid addition salts of those compounds having basic nitrogen atoms in association with pharmaceutical carriers or diluents. The compounds possess antiphlogistic activity.
GB3871272A 1971-08-20 1972-08-18 4-4-biphenylyl - butyramides Expired GB1396748A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE2141926A DE2141926A1 (en) 1971-08-20 1971-08-20 4-(4-biphenylyl)-4-hydroxybutyramide derivs - with antiphlogistic activity
DE2141925A DE2141925A1 (en) 1971-08-20 1971-08-20 4-(4-biphenylyl)-4-oxobutyramides - with antiphlogistic activity
DE2141927A DE2141927A1 (en) 1971-08-20 1971-08-20 4-(4-biphenylyl)-butyramide derivs - with antiphlogistic activity

Publications (1)

Publication Number Publication Date
GB1396748A true GB1396748A (en) 1975-06-04

Family

ID=27183652

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3871272A Expired GB1396748A (en) 1971-08-20 1972-08-18 4-4-biphenylyl - butyramides

Country Status (6)

Country Link
US (1) US3882174A (en)
BE (1) BE787782A (en)
FR (1) FR2150809B1 (en)
GB (1) GB1396748A (en)
IL (1) IL40161A0 (en)
NL (1) NL7211363A (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATA785173A (en) * 1972-08-17 1975-01-15 Thomae Gmbh Dr K PROCESS FOR PREPARING NEW 4- (4-BIPHENYLYL) -4-HYDROXY-BUTTERIC ACID AMIDES
US4060533A (en) * 1976-06-25 1977-11-29 Sandoz, Inc. Pyranone carboxamides
IL115995A0 (en) * 1994-11-15 1996-01-31 Bayer Ag Substituted 4-biarylbutyric or 5-biarylpentanoic acids and derivatives as matrix metalloprotease inhibitors
US5789434A (en) * 1994-11-15 1998-08-04 Bayer Corporation Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors
MXPA03011558A (en) * 2001-06-12 2004-03-26 Wellstat Therapeutics Corp Compounds for the treatment of metabolic disorders.
CN105085433B (en) * 2014-05-19 2019-06-25 中国科学院上海药物研究所 Substituted amide phenol compound and preparation method thereof, pharmaceutical composition and purposes

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3624142A (en) * 1964-09-10 1971-11-30 Merck & Co Inc Substituted biphenyl acetic acid derivatives

Also Published As

Publication number Publication date
IL40161A0 (en) 1972-10-29
US3882174A (en) 1975-05-06
NL7211363A (en) 1973-02-22
FR2150809B1 (en) 1976-03-05
BE787782A (en) 1973-02-19
FR2150809A1 (en) 1973-04-13

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Legal Events

Date Code Title Description
CSNS Application of which complete specification have been accepted and published, but patent is not sealed